15 nights/ 16 days
Athens to Athens

The Cyclades archipelago is comprised of about 220 islands in the Aegean Sea – the most well-known being Mykonos and Santorini. A yacht adventure is the ideal way to experience what many consider to be the world’s most beautiful islands. We’ll have our own private sailing yacht with an experienced crew. There will be plenty of time for hiking, snorkeling, kayaking and relaxing as we explore ancient archaeological sites and taverna-lined harbors. We’ll enjoy breakfast and lunch on the boat daily. Evening meals are a cultural and gastronomical experience on this adventure. We’ll dine at a different island each night and enjoy a wonderful selection of fresh seafood and local cuisine. Don’t forget to try the ouzo!

2017 Dates: May 26-June 10 $3395 $2850 (Single Supplement N/A)
Trip Leader(s):Stacey + Local Skipper & Assistant
Places Visited:Athens, Siros, Mykonos, Paros, Koufonisi, Santorini, Ios, Sifnos, Kithnos
Activities:Sailing, hiking, kayaking, snorkeling, sightseeing
Group Size:Min. 6 Max. 8
Travel Style:Comfort/ Sailing
Physical Rating:All Ability Levels

Ready to book? Please click the button below to BOOK THIS TRIP and submit your information along with a $500 deposit.  Your deposit is fully refundable for 72 hours and always transferable to any of our other trips, or we can hold it for a future trip.

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  • Sail the beautiful Greek Islands from Athens for 14 days on a private 50 foot sailing yacht with an experienced crew and try your hand at sailing, or just relax on deck
  • Enjoy authentic Greek food and fresh seafood in waterfront tavernas
  • Swim and snorkel in the warm Mediterranean waters off the side of the boat and let the waves rock you to sleep each night
  • Star gaze from the deck of our yacht or the shore lined beaches
  • Explore the whitewashed villages of Santorini, the most popular island in Greece, if not the world


Our sailing vessel is a Beneteau Cyclades 50.5 monohull sloop with 4 double cabins (+ 2 crew quarters) and 3 washrooms. Your chartered yacht will include an experienced skipper and an assistant who will provide two healthy meals aboard the yacht each day. There is no kitty, or deciding who is going to make the meals or wash the dishes!

Note: Images shown are of the make/ model of the yacht we’ll be sailing, not the actual yacht. On occasion, based upon the number of bookings, a different vessel, either larger or smaller, could be used. The service, meals, and itinerary are not changed when a vessel changes.

Day 1: Athens

Today is arrival day so there are no activities planned. You are free to relax or explore the city. Athens is the historical capital of Europe, with a long history, dating from the first settlement in the Neolithic age, 5th Century BC.  Our hotel will be located near the Acropolis and is surrounded by small art museums, galleries, jewelry museums, cafes and restaurants.

Overnight at Hotel Herodion or similar

Day 2: Athens to Lavrion Marina (B)

This morning, after checking out of the hotel, we’ll head to the Lavrion Marina where we will leave our bags in the marina office and spend the afternoon exploring this area. Located on the tip of the Attiki Peninsula, the oldest and biggest ancient amphitheater in the country is located here as well as a mysterious giant hole that would be an attraction to Fortians and seekers of unexplained phenomena if they knew about it.

The afternoon is free to do whatever you choose before boarding our yacht at 5:00pm. Upon boarding, we’ll be greeted by our crew who will be with us for the next fourteen days. After unpacking our belongings, we’ll receive a safety briefing in the cockpit followed by a relaxed welcome dinner (not included) at one of the many nearby tavernas, giving you an opportunity to get to know our crew a bit better.

We’ll spend the night on the boat this evening in the marina so that we can depart early in the morning.

–Private transfer from Athens to Lavrion Marina
–Meals: Breakfast

Overnight on the boat at Lavrion Marina

Day 3: Lavrion to Syros (B, L)

This morning, we’ll depart the marina very early since we have a long day of sailing ahead of us. The journey through the marvelous islands of the Cyclades is illuminated by the blue and white colors of the Aegean. According to ancient myth, it is Poseidon, God of the sea, who created the island complex that is now one of the most famous worldwide. The Cycladic islands charm and challenge all sea lovers. It is within their crystal-clear waters that senses awake to allow travelers to grasp the essence of the islands’ splendor.

We’ll arrive in the afternoon to the island of Syros, the island where Greek tradition and western influence come to a harmonious marriage.  After stepping off the yacht, a visit to both the Catholic and Orthodox cathedrals on their respective hills offers a great view back down to the harbor. The great number of beautiful beaches will delight the sea and sand lovers.

Syros is well-known for its gastronomic peculiarities. Halva pie (a pie made of thyme honey and roasted almonds), loukoumi (a delight made of water, starch and sugar), “loosa” ham, fennel sausages, and the San Mihalis spicy cheese will no doubt satisfy even the most demanding taste buds. In the evening, we’ll enjoy dinner at one of the beautiful garden tavernas.

–Meals: Breakfast & Lunch (on the boat)

Distance from Lavrion to Syros: 46 NM – 9 hours
Overnight on the boat at Syros Island

Day 4: Syros to Mykonos (B, L)

After breakfast, we’ll motor along the coastline and then set sail to Greece’s most famous cosmopolitan island, a whitewashed paradise in the heart of the Cyclades. According to mythology, Mykonos was formed from the petrified bodies of giants killed by Hercules. It gets its name from the grandson of Apollo, “Mykonos.”

Stroll around its narrow marble streets and admire whitewashed houses with colorful doors and window frames, bougainvillea trees in purple bloom and hidden churches. Soak up the atmosphere along the lively waterfront and admire a fleet of fishing boats casting colorful reflections in the azure waters. One of the most scenic corners of the island is Alefkantra or “Little Venice,” an 18th century district, dominated by grand captains’ mansions with colorful balconies and stylish windows.

While you’re out strolling, don’t be surprised if you come across the official mascot of Mykonos, which is nothing other than a… pelican! Petros the Pelican was found by a fisherman after a storm in 1954, and eventually became the locals’ companion. When he died, the grief for his loss was so deep that a replacement was soon found. In honor of Petros, the locals have established a long tradition of pelicans wandering around the waterfront as an essential part of everyday life. So, whatever you do, don’t forget to take a picture with the successor of the famous pelican Petros!

In the evening, we’ll enjoy a group dinner (not included) at one of the rooftop garden tavernas. Enjoy some local Aegean specialties such as Pepper flavored kopanisti, a soft cheese seasoned with pepper. It is the island’s gastronomic trademark. Try it as a topping on a round rusk spread with grated tomato, a favorite local appetizer. Meat eaters can sample “louzes” (cooked pork filet with spices) and tasty local sausages sprinkled with pepper, and local oregano that has been caressed by the sun and dried in the north wind. To finish off your meal you can sample two exceptionally good local pastries, “amigdalota” (small round cakes with ground almond, rosewater and caster sugar) and honey pie.

If you’re up for it, be sure take advantage of Mykonos’ world renowned party scene.

–Meals: Breakfast & Lunch (on the boat)

Distance from Syros to Mykonos: 25 NM – 5 hours
Overnight on the boat at Mykonos Island

Day 5: Mykonos (B, L)

Today, enjoy a full day at your leisure in Mykonos, and perhaps try your hand at one of the islands numerous water sports. It is only natural that the “Island of Winds” should attract surfers and sailors from all over the world! There is a great choice of beaches for windsurfing; however, the most secluded ones are considered to be the best. Choose from Korfos, Ftelia, Meyali Ammos and Kalafatis, where surfing lessons are also available. Play beach volleyball at Ayia Anna or try sea parachuting or jet skiing at Elia or Kalafatis.

Diving fans can do a little exciting exploration of the underwater magic of Mykonos. On the island, you can find many well-organized diving centers. Explore the island on a cacique or a boat and discover secluded beaches, or take a boat tour around the nearby islets, which are also ideal fishing spots!

Be sure to hit the rooftop of the Belvedere Hotel to watch the sunset and try their Lychee Mojito. You won’t regret it!

–Meals: Breakfast and Lunch (on the boat)

Overnight on the boat at Mykonos Island

Day 6: Mykonos to Paros (B, L)

Unrivalled natural beauty, beaches with crystal clear waters, unrivalled Byzantine footpaths connecting traditional villages and breathtaking landscapes make up the island of Paros, located in the heart of the Cyclades. Parikia, the capital of Paros, is a beautiful Cycladic village with whitewashed cubic houses and impressive neoclassical mansions. A well preserved 13th century Venetian castle stands proudly on a hill at the center of the village offering an amazing view of Parikia. Here, you’ll also find the 6th century church of Panayia Ekatontapyliani, also called Katapoliani. The name “Ekatontapyliani” means the church with 100 gates, one of which is a secret one!

Sun-drenched beaches, like Chirssi Akti, Santa Maria and Pounda, welcome sun-loving visitors who want to enjoy the crystal-clear sea, the sun or even their favorite water sports. You may also choose to discover the island’s stunning beauty by hiking along the “strates,” the trails created by farmers to help them cross the island and transport their goods. It’s like stepping back into history! Alternatively, you can discover the island on horseback. There are two horse-riding centers, one by the sea at Ambelas, and one at Ysterni. Ride around the coast, along the sandy beaches or take a detour inland – a great way for you to discover some of the most beautiful spots on the island.

–Meals: Breakfast and Lunch (on the boat)

Distance from Mykonos to Paros: 25 NM – 5 hours
Overnight on the boat at Paros

Day 7: Paros to Koufonisi (B, L)

Koufonisia is a small group of two islands, Pano Koufonisi (Upper Koufonisi) and Kato Koufonisi (Lower Koufonisi), that are separated by a narrow strait. They were named Koufonisia (meaning Hollow islands) because of the existing huge caves which gave the impression to pirates who viewed them from a distance that the islands were hollow.

Upon arrival, we’ll motor around the island and admire the sea caves as well as the nearby islets Glaronisi, Prasoura, Voulgari, Tsouloufi, Lazaros and Megali Plaka; all of them have been designated as areas of great natural beauty.

After docking, we’ll see the white windmill which stands at the harbor entrance as if welcoming visitors. Chora is further up, a typical Cyclades village with white-washed houses and picturesque alleys. In the center, you’ll see Agios Georgios church, the island’s patron saint.

Koufonisia is the perfect place to relax on one of the golden sand beaches, swim in one of the small natural pools of turquoise waters, or rent a bicycle and tour the island following the shoreline. Visit the inland area and hike along the paths from Chora to Pano Meria.

For dinner, we’ll feast at one of the local tavernas, the original ‘island way,’ and enjoy seafood fresh from the sea.

–Meals: Breakfast and Lunch (on the boat)

Distance from Paros to Koufonisi: 27 NM – 6 hours
Overnight on the boat at Koufonisi

Day 8: Koufonisi to Santorini (B, L)

Today will be another full day of sailing as we make our way to Santorini! Santorini is the most popular island in Greece, if not the world. In fact, it’s actually a group of islands consisting of Thira, Thirassia, Aspronissi, Palea and Nea Kameni. It is frequently included among the best destinations in the world. There are few travel destinations that combine beautiful beaches, spectacular scenery, ancient cities, amazing restaurants, some of the world’s best wine, and an active volcano. The entire complex of Santorini islands is still an active volcano and probably the only volcano in the world whose crater is in the sea. The last big eruption occurred 3,600 years ago and what remains today is a submerged volcano and a caldera.

Amazing villages have been constructed on the edge of this caldera, with Cycladic architecture and breathtaking views and sunsets. Fira is the picturesque capital of the island; perched high up on the edge of the Caldera, it looks like a marvelous painting. Fira, together with Oia, Imerovigli and Firostefani, located high above on a cliff, make up the so-called “Caldera’s eyebrow,” the balcony of Santorini, which offers an amazing view of the volcano. Some of the villages are cosmopolitan and some more peaceful, surrounded by vast vineyards, whitewashed cliff-top towns with castles affording amazing views out over the Aegean.

A visit to Santorini is the ultimate gastronomic experience, as the island is a true culinary paradise! Treat your taste buds to some famous traditional products like cherry tomatoes, white egg plants, fava, caper and “hloro tyri,” a special kind of fresh goat cheese found on the island, or why not try some of the exceptional wines produced from grapes grown in the volcanic soil.

–Meals: Breakfast and Lunch (on the boat)

Distance from Koufonisi to Santorini: 46 NM – 9 hours
Overnight on the boat at Santorini

Day 9: Santorini (B, L)

Today is free to explore the island at your leisure. Whether you choose to participate in water sports or trekking activities, visit museums, shop, or simply relax on the beach, the possibilities are endless!

Santorini is especially known for its natural beauty and is ideal for nature lovers. It offers a lot of amazing paths to do some trekking to view wild, volcanic landscapes to picturesque villages and lovely churches in the countryside. Trekking is a great way to get to know the island in a more special way. There are numerous routes that vary in length and difficulty for anyone to enjoy.

Venture into Santorini’s seaside treasures and enjoy deep blue waters and beaches with white, red or black sand or volcanic pebbles, spectacular rock formations and impressive lunar landscapes.

Take a full-day or half-day kayaking tour, get a birds-eye view of the island by taking a parasailing excursion, explore the island on an ATV, take off on a jet ski, or try a water skiing lesson. Most beaches in Santorini have a water sports center with loads of fun activities to choose from.

–Meals: Breakfast and Lunch (on the boat)

Overnight on the boat at Santorini

Day 10: Santorini to Ios (B, L)

Ios or Nios, as the locals call it, is one of the most beautiful islands of the Cyclades, like a flower, as its name “Ion” denotes. According to the ancient tradition, Ios was the homeland of Homer’s mother and the final resting place of the great epic poet.

Upon reaching the island, the village of Hora is enchanting and as pretty-as-a-picture. The snow-white little houses, picturesque arcade-covered alleys, the twelve windmills, churches with arched belfries and light blue domes create a unique residential area. Out of the 365 churches on the island, the most important is Panayia Gremiotissa, standing on Hora’s highest spot. It is built literally on the edge of a cliff, affording an amazing view of the open sea.

A feast of local tastes awaits lucky visitors: chickpea balls, sun-dried picarel, tsimetia (stuffed vegetable marrow flowers), vegetable marrow omelette, dolmadakia using fresh vine leaves from the numerous vineyards where the famed niotiko wine is produced, and goat soup are just a few of the menu items we might find at dinner this evening.

Don’t leave without getting some of the local cheeses like skotiri (soft goat cheese with herbs), local kefalotyri (hard salty yellow cheese) and mizithra (soft white creamy, almost sweet cheese) as well as some of the excellent thyme honey, pastelia (honeyed sesame bars), watermelon confiture, mizithra pie and pomegranate liqueur.

–Meals: Breakfast and Lunch (on the boat)

Distance from Santorini to Ios: 30 NM – 5 hours
Overnight on the boat at Ios

Day 11: Ios to Sifnos (B, L)

Sifnos, the island of flavors, is the birthplace of several famous poets, such as Ioannis Gryparis, Kleanthis Triantafyllou (or Rampagas) and Aristomenis Provelegios; as well as award-winning chefs like Tselementes. Unique traditional villages, organized and secluded beaches, and 227 churches spread around the island are waiting to be discovered.

Apollonia, the capital town of Sifnos, is built in the shape of an amphitheater over three hills in the center of the island. During your evening walk, be sure to pay a visit to the Folklore Museum at the Hiroon Square (meaning “Square of the Heroes”).

A few kilometers away from the town lies the traditional settlement of Artemonas, famous for its neoclassic mansions and its outstanding panoramic view of the island. Some of the most famous restaurants and patisseries of Sifnos will welcome you here with fresh homemade cookies and hot doughnuts.

The historic settlement of Kastro (meaning “castle”), inhabited since ancient times, is built over the ruins of ancient Sifnos, on an abrupt rock with a breathtaking view of the sea. A beautiful outdoor museum and one of the most picturesque villages on the island, Kastro stands out for its old houses with the wooden balconies, the ancient columns and the narrow courtyards.

Whether cosmopolitan or secluded, all the beaches in Sífnos offer sun-loving tourists azure waters and sun-drenched sandy beaches. Kamáres, the port of the island, is a sandy beach with trees and beach bars; Platís Yialós is the most cosmopolitan and buzzing beach on the island, whereas next to it lies Vathí, a sandy beach with shallow waters and many tavernas where you can enjoy fresh fish. The rocks in Chrisopigí, where also the homonymous Monastery proudly stands, are ideal for diving. If you’d like to rest under a cool shade, head to the next beach which is surrounded by salt water loving trees. If you find yourself in Kástro, follow down the path to “Eptá Mártyres”, and enjoy a leisurely swim or unwind with a book lazing on a sun lounger.

Sifnos is the center of pottery in the Cyclades since the first samples were found here are dated back to the Early Cycladic period. The island’s clay soil in combination with the continuous sunshine resulted in the development of the art of pottery on the island. Throughout the island there are many pottery workshops where you can buy ceramics for domestic use, utensils and decorative items.

In every small taverna or classy restaurant, you can sample some of Sifnos’ exceptional dishes cooked by chefs who know how to tempt our taste buds. When the night falls, set out to discover fancy lounge bars and the hottest nightclubs on the island and dance the night away!

–Meals: Breakfast and Lunch (on the boat)

Distance from Ios to Sifnos: 30 NM – 5 hours
Overnight on the boat at Sifnos

Day 12: Sifnos to Serifos (B, L)

Serifos Island, with its rugged mining sites, ladened with history, has its own distinct Cycladic flair. The island exudes a calm atmosphere and speaks directly to our senses. The locals have respected the Cycladic architectural tradition by building white and blue houses making the islands towns and villages all the more powerful. There is much to do here including hiking, climbing, mountain biking and diving!

Beach-goers will have plenty of beaches to choose from while visiting Serifos Island; rocky, pebbly, or sandy beaches accompanied by crystal blue waters will satisfy all tastes. Beaches are reached either by car, walking trails or by sea.

Serifos’ cuisine bursts with aromas and flavors! Try delicious meat products such as louzes, syglina (traditional cured pork) and sausages, as well as the islands rich aromatic spices. Taste marathopites and marathotiganites (fennel pies, baked or fried), revythada (traditionally cooked chickpeas) with a local variety of raisins, sun-dried octopus, local cheeses sucha as myzithres and xinomyzithres. Make sure to accompany your meal with the islands local wines.

–Meals: Breakfast and Lunch (on the boat)

Distance from Sifnos to Serifos: 20 NM – 4 hours
Overnight on the boat at Serifos

Day 13: Serifos to Kythnos (B, L)

Kythnos, also called “Thermia” on the account of its thermal springs, is in the Western Cyclades. It is a surprising island of beautiful beaches, traditional villages, and folding hills punctuated by stone huts and ancient walls. An agricultural island mostly, life is still simple. We’ll arrive at the rustic fishing village of Merihas. The harbor is a safe and quaint place with an open-air fish market, restaurants strung along a sandy beach, an internet cafe and ice cream parlor. To cool off, we’ll have a swim at the tiny little beach just 5-minutes’ walk from the yacht.

The most impressive of the 65 sandy beaches is the island of Kolona, where a lane of sand connects the islet of Ayios Loukas to Kythnos. Low stone fences run for many kilometers on bare Cycladic hills with 350 white country chapels here and there. The typical Cycladic style equally appears in the villages with its cobbled narrow streets, white houses, squares, chapel and windmills. Follow the paths that connect the villages to each other and taste apricots and wild mulberries on the way to Katafyki cave, one of the biggest caves in Greece with beautiful stalactites and stalagmites.

–Meals: Breakfast and Lunch (on the boat)

Distance from Serifos to Kythnos: 24 NM – 5 hours
Overnight on the boat at Kythnos

Day 14: Kythnos (B, L)

On the northeastern coast of the island, the village of Loutra is famous for its thermal hot springs, which boast healing powers, as well as a rather special archaeologic interest on the island called Maroulas. It is the home to one of the oldest prehistoric Mesolithic archaeological settlements in all of the Cyclades, dating between 9000-8000 BC. The excavations, which ended in 2005, unearthed 30 round spaces that used to be hut floors. 15 tombs, one of which contained a human skeleton and tools made of pyrite, obsidian, and quartz, were found below their stone layers.

After a visit to the archaeological site, why not visit the thermal spa center (optional) and relax in the swimming pool, try a hammam (Turkish bath) or sauna, or get a hydro massage? This modern spa is located on a cliff overlooking the Aegean Sea.

–Meals: Breakfast and Lunch (on the boat)

Overnight on the boat at Kythnos

Day 15: Kythnos to Lavrion Marina (B, L)

Today, we’ll make our way back to Athens arriving in the harbor in the afternoon and we’ll say our goodbyes to our crew before disembarking the yacht. We’ll have private transportation to take us back to the city for our last night with the group.

–Meals: Breakfast and Lunch (on the boat)

Distance from Kythnos to Lavrion Marina: 25 NM – 5 hours

Overnight at Hotel Herodion or similar

Day 16: Athens (B)

Today is departure day and there are no planned activities as we say goodbye to our new friends and head home or to your next destination.

–Meals: Breakfast

What’s Included?

2 nights (4*) hotel/ 13 nights aboard a 50ft yacht
Fully licensed skipper & crew
All meals indicated in the itinerary (B=Breakfast, L= Lunch, D=Dinner)
All transfers listed in the itinerary
On-Board Snorkeling Equipment
On-Board Kayaks
Yacht cleaning service
Fuel Costs
Marina Fees

What’s Not Included?

International airfare to Athens
Airport taxes & excess baggage fees
Travel Insurance
Alcoholic beverages & meals not specified
Personal expenses
Optional Activities

The information in this trip details document has been compiled with care and is provided in good faith. However, it is subject to change, and does not form a contract between parties. While it is our intention to adhere to the route described, there is a certain amount of flexibility built into the itinerary and on occasion it may be necessary, or desirable to make alterations. The itinerary is brief, as we never know exactly where our journey will take us. Due to our style of travel and the regions we visit, travel can be unpredictable. Occasionally our itineraries change due to weather or other circumstances that are beyond our control. Additionally, any travel times listed are approximations only and subject to vary.

This is a real sailing trip and you must be comfortable with moving about the boat. Yachts are designed to maximize living area space, so sleeping quarters can be a bit cramped. For solo travelers, there is no single supplement on-board the yacht. You will be paired with a same sex roommate.

Please be aware that this is a sailboat and not a cruise vessel and space on board is tight. You will be sharing a small room with one of your fellow travelers or your travel partner and possibly sharing a bathroom onboard. Some people are not comfortable with the type of close quarter arrangements typically found on sailboats, however if a real sailing experience on a real sailboat is what you are after, then this experience should more than make up for cramped quarters.

That said, the adventure and exhilaration of an authentic sailing trip more than makes up for any discomfort. Although the waters are usually calm, it can get rough and choppy, which requires steady sea legs and a sturdy stomach. Rain or shine, your trusty crew will always be on hand to assist you.

Also, If you do enjoy a late night out, consider booking a hostel for the night so you don’t wake other travelers (and more importantly the skipper) upon your return. It’s important to have fun, but also to respect your shipmates who might be sleeping.

The Cyclades lie to the southeast of Athens and the Greek mainland and to the east/ southeast of Poros. Unlike the Saronic Gulf, the Cyclades islands are not protected by any mainland. Their position out into the Aegean Sea means they are more exposed to the northerly ‘Meltemi’ wind which very much dominates the Cyclades islands from late July to September. These wind conditions mean sailing the Cyclades islands provides for more invigorating sailing, but might also prove ‘too exciting’ for those looking for something more mellow.

Trip Length
15 nights/ 16 days
Travel Style
Comfort/ Sailing
Physical Rating
All Ability Levels
Starting at $3395